How to have high-value conversations

There is nothing wrong with entertainment if entertainment is what you want. But people often switch to entertainment automatically just because it's easy and immediately socially rewarding.

It's like a difference between reading internet once in a while, and spending your whole day online. There should be an "internet" time, but also a "non-internet" time. Similarly, in social situations we want to have both "entertainment" time and "non-entertainment" time.

In the spirit of purchasing fuzzies and utilons separately, perhaps we should try to make separate time slots for maximum entertainment (fun and group bonding) and time slots for maximum becoming stronger. As opposed to having mediocre insights interrupted by jokes and board games.

(As an extreme example, two hours of group sex followed by two hours of high-quality quantum physics lessons would give you both more pleasure and more knowledge than four hours of playing Monopoly and having small talk.)

I'm not saying that all conversations should be steered towards insight, but more of them should be, especially in the rationalist community, where the potential value of conversations is high. There is nothing wrong with entertainment per se, but conversations gravitate towards entertainment by themselves more often than not.

You should have recorded them, might change your opinion. The effect of discussing subjectively deep shit is even worse with weed and LSD.

Thanks for the great links! I agree that getting people to feel comfortable is really important for having good conversations. The list of questions in my post is intended to find personal topics that would be of common interest, but I think it's much more likely to work if the people involved are already feeling comfortable with each other.

Your CouchSurfing experience reminds me of a class at Burning Man where people were split up into pairs, and tried to take the shortest conversational path to getting to know each other. There was a built-in affordance to ask personal questions about feelings though, since everyone was in the class with that purpose. Did you end up developing patterned ways to ask strangers about they thought and felt without it feeling awkward?

I find that there is a self-signaling aspect to this: "if I'm staying up late to have this conversation, it must be interesting / important".

This sounds like crap a teacher would ask their class or a psychiatrist would ask their patient to elicit responses. Robotic, unfun, and vague.

I suspect the bad feelings come from the experience that the teacher usually does not care about things that I care about. So I am asked to give a response of a very specific type, or I will be punished (socially).

Contrast this with an environment where speaking about unusual things may be socially rewarded, and admitting your weakness may lead to a rational advice how to fix it.

Sometimes people learn that the best way to avoid being hurt is to avoid being open. That's a good advice for a harmful environment. It's not an optimal behavior in helpful environment.

I have tried around half of these questions. I have asked "what have you been thinking about lately?" a couple of times, and found out about a project a friend was working on, for example. Asking what people have been reading led to learning about what people have been reading, which was interesting. Some of the questions were posed to me, like "what memes have affected you?" and "what surprised you?", and I found them to affect the conversation positively (in the former case, we ended up discussing the effect of the diligence meme on my early life).

I agree that a lot of these require some leadup. For example, the question "what eccentric things have you done?" might come naturally after telling people about your skydiving trip last week. Vagueness is partly addressed by the "recently/lately" specification, but I agree that the questions could use some further narrowing down. Do you have any suggestions to that end?